Chlorotrimethylsilane → HCID 12953067, compound

HRID 904560Notes

Reaction equation

HRID 904560 reaction equation
Cl[Si](C)(C)C.[O:6]=[C:7]1[N:12]2[CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=[CH:16][C:11]2=[N:10][C:9]2[CH2:20][S:21][CH2:22][C:8]1=2.ClN1C(=O)CCC1=O>N1C=CC=CC=1.O>[O:6]=[C:7]1[N:12]2[CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=[CH:16][C:11]2=[N:10][C:9]2=[CH:20][S:21][CH:22]=[C:8]12

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 31398ChlorosuccinimideHCID 12953042HCID 12953042, compound

Product 1

HCID 12953067HCID 12953067, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Chlorotrimethylsilane (2.6 ml, 0.02 mol) is added to a cooled (icebath) solution of 3,10-dihydro-10-oxo-1H-pyrido[1,2-a]thieno[3,4-d]pyrimidine-7-carboxylic acid (5.0 g., 0.02 mol) in pyridine (40 ml) under nitrogen. The mixture is stirred at ice bath temperature for one hour and then allowed to warm to room temperature. N-Chlorosuccinimide (2.74 g., 0.02 mol) is added and the mixture is heated at 90°-95° C. for 20 minutes. The mixture is cooled, diluted with water (5 ml) and stirred for 15 minutes. The precipitate is filtered off, dried, washed with boiling acetone (3×100 ml) and recrystallized from dimethylformamide to give the product (3.9 g.), mp 320° C. (dec).

Workup

  1. temperaturethe mixture is heated at 90°-95° C. for 20 minutes
  2. temperatureThe mixture is cooled
  3. stirringstirred for 15 minutes
  4. filtrationThe precipitate is filtered off
  5. customdried
  6. washwashed with boiling acetone (3×100 ml)
  7. customrecrystallized from dimethylformamide
  8. customto give the product (3.9 g.), mp 320° C. (dec)

Sources & evidence

ORD record
ord-99cf641e97644be9af13873f6684e2b2
Source dataset
uspto-grants-1980_10
Patent number
US04230707

Reaction notes

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